Phosphine

Chemical compound hydrogen phosphide

This article is about PH3. For organic derivatives, see Organophosphine. For the visual phenomenon, see phosphene. For the star, see Kepler-289.

Not to be confused with phosgene.

Phosphine  Skeletal formula of phosphine

| Ball-and-stick model of phosphine | Spacefill model of phosphine

Phosphorus, P

Hydrogen, H

|

Names
IUPAC name

Phosphane

Other names

Hydrogen phosphide
Phosphamine
Phosphorus trihydride
Phosphorated hydrogen

Identifiers

CAS Number

* 7803-51-2 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:30278 Y

ChemSpider |

* 22814 Y

ECHA InfoCard | 100.029.328
EC Number |

* 232-260-8

Gmelin Reference

| 287

PubChem CID

* 24404

RTECS number |

* SY7525000

UNII |

* FW6947296I Y

UN number | 2199

CompTox Dashboard (EPA)

* DTXSID2021157

InChI

* InChI=1S/H3P/h1H3 Y

Key: XYFCBTPGUUZFHI-UHFFFAOYSA-N Y

* InChI=1/H3P/h1H3

Key: XYFCBTPGUUZFHI-UHFFFAOYAP

SMILES

* P

Properties

Chemical formula

| PH3
Molar mass | 33.99758 g/mol
Appearance  | Colourless gas
Odor | odorless as pure compound; fish-like or garlic-like commercially[1]
Density | 1.379 g/L, gas (25 °C)
Melting point | −132.8 °C (−207.0 °F; 140.3 K)
Boiling point | −87.7 °C (−125.9 °F; 185.5 K)

Solubility in water

| 31.2 mg/100 ml (17 °C)
Solubility | Soluble in alcohol, ether, CS2
slightly soluble in benzene, chloroform, ethanol
Vapor pressure | 41.3 atm (20 °C)[1]
Conjugate acid | Phosphonium (PH+4)

Refractive index (nD)

| 2.144
Viscosity | 1.1×10−5 Pa⋅s
Structure

Molecular shape

| Trigonal pyramidal

Dipole moment

| 0.58 D
Thermochemistry

Heat capacity (C)

| 37 J/mol⋅K

Std molar
entropy (S⦵298)

| 210 J/mol⋅K[2]

Std enthalpy of
formation (ΔfH⦵298)

| 5 kJ/mol[2]

Gibbs free energy (ΔfG⦵)

| 13 kJ/mol
Hazards
GHS labelling:

Pictograms

NFPA 704 (fire diamond)  |

Flash point | Flammable gas

Autoignition
temperature

| 38 °C (100 °F; 311 K) (see text)
Explosive limits | 1.79–98%[1]
Lethal dose or concentration (LD, LC):

LD50 (median dose)

| 3.03 mg/kg (rat, oral)

LC50 (median concentration)

| 11 ppm (rat, 4 hr)[3]

LCLo (lowest published)

| 1000 ppm (mammal, 5 min)
270 ppm (mouse, 2 hr)
100 ppm (guinea pig, 4 hr)
50 ppm (cat, 2 hr)
2500 ppm (rabbit, 20 min)
1000 ppm (human, 5 min)[3]
NIOSH (US health exposure limits):

PEL (Permissible)

| TWA 0.3 ppm (0.4 mg/m3)[1]

REL (Recommended)

| TWA 0.3 ppm (0.4 mg/m3), ST 1 ppm (1 mg/m3)[1]

IDLH (Immediate danger)

| 50 ppm[1]
Safety data sheet (SDS)  | ICSC 0694
Related compounds

Other cations

* Ammonia
* Arsine
* Stibine
* Bismuthine

Related compounds

* Trimethylphosphine
* Triphenylphosphine

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)

Infobox references

Chemical compound

Phosphine (IUPAC name: phosphane) is a colorless, flammable, highly toxic compound with the chemical formula PH3, classed as a pnictogen hydride. Pure phosphine is odorless, but technical grade samples have a highly unpleasant odor like rotting fish, due to the presence of substituted phosphine and diphosphane (P2H4). With traces of P2H4 present, PH3 is spontaneously flammable in air (pyrophoric), burning with a luminous flame. Phosphine is a highly toxic respiratory poison, and is immediately dangerous to life or health at 50 ppm. Phosphine has a trigonal pyramidal structure.

Phosphines are compounds that include PH3 and the organophosphines, which are derived from PH3 by substituting one or more hydrogen atoms with organic groups.[4] They have the general formula PH3−nRn. Phosphanes are saturated phosphorus hydrides of the form PnHn+2, such as triphosphane.[5] Phosphine (PH3) is the smallest of the phosphines and the smallest of the phosphanes.

## History

[edit]

Philippe Gengembre (1764–1838), a student of Lavoisier, first obtained phosphine in 1783 by heating white phosphorus in an aqueous solution of potash (potassium carbonate).[6][NB 1]

Perhaps because of its strong association with elemental phosphorus, phosphine was once regarded as a gaseous form of the element, but Lavoisier (1789) recognised it as a combination of phosphorus with hydrogen and described it as phosphure d'hydrogène (phosphide of hydrogen).[NB 2]

In 1844, Paul Thénard, son of the French chemist Louis Jacques Thénard, used a cold trap to separate diphosphine from phosphine that had been generated from calcium phosphide, thereby demonstrating that P2H4 is responsible for spontaneous flammability associated with PH3, and also for the characteristic orange/brown color that can form on surfaces, which is a polymerisation product.[7] He considered diphosphine's formula to be PH2, and thus an intermediate between elemental phosphorus, the higher polymers, and phosphine. Calcium phosphide (nominally Ca3P2) produces more P2H4 than other phosphides because of the preponderance of P-P bonds in the starting material.

The name "phosphine" was first used for organophosphorus compounds in 1857, being analogous to organic amines (NR3).[NB 3][8] The gas PH3 was named "phosphine" by 1865 (or earlier).[9]

## Structure and reactions

[edit]

PH3 is a trigonal pyramidal molecule with C3v molecular symmetry. The length of the P−H bond is 1.42 Å, the H−P−H bond angles are 93.5°. The dipole moment is 0.58 D, which increases with substitution of methyl groups in the series: CH3PH2, 1.10 D; (CH3)2PH, 1.23 D; (CH3)3P, 1.19 D. In contrast, the dipole moments of amines decrease with substitution, starting with ammonia, which has a dipole moment of 1.47 D. The low dipole moment and almost orthogonal bond angles lead to the conclusion that in PH3 the P−H bonds are almost entirely pσ(P) – sσ(H) and phosphorus 3s orbital contributes little to the P-H bonding. For this reason, the lone pair on phosphorus is predominantly formed by the 3s orbital of phosphorus. The upfield chemical shift of its 31P NMR signal accords with the conclusion that the lone pair electrons occupy the 3s orbital (Fluck, 1973). This electronic structure leads to a lack of nucleophilicity in general and lack of basicity in particular (pKaH = −14),[10] as well as an ability to form only weak hydrogen bonds.[11]

The aqueous solubility of PH3 is slight: 0.22 cm3 of gas dissolves in 1 cm3 of water. Phosphine dissolves more readily in non-polar solvents than in water because of the non-polar P−H bonds. It is technically amphoteric in water, but acid and base activity is poor. Proton exchange proceeds via a phosphonium (PH+4) ion in acidic solutions and via phosphanide (PH−2) at high pH, with equilibrium constants Kb = 4×10−28 and Ka = 41.6×10−29. Phosphine reacts with water only at high pressure and temperature, producing phosphoric acid and hydrogen:[12][13]

PH3 \+ 4H2O pressure & temperature→ H3PO4 \+ 4H2.

Burning phosphine in the air produces phosphoric acid:[14][12]

PH3 \+ 2 O2 150°C→ H3PO4.

## Preparation and occurrence

[edit]

Phosphine may be prepared in a variety of ways.[15] Industrially it can be made by the reaction of white phosphorus with sodium or potassium hydroxide, producing potassium or sodium hypophosphite as a by-product.

3 KOH + P4 \+ 3 H2O → 3 KH2PO2 \+ PH3

3 NaOH + P4 \+ 3 H2O → 3 NaH2PO2 \+ PH3

Alternatively, the acid-catalyzed disproportionation of white phosphorus yields phosphoric acid and phosphine. Both routes have industrial significance; the acid route is the preferred method if further reaction of the phosphine to substituted phosphines is needed. The acid route requires purification and pressurizing.

### Laboratory routes

[edit]

It is prepared in the laboratory by disproportionation of phosphorous acid:[16]

4 H3PO3 → PH3 \+ 3 H3PO4 Phosphine evolution occurs at around 200 °C.

Alternative methods are the hydrolysis zinc phosphide:

Zn3P2 \+ 6 H2O → 3 Zn(OH)2 \+ 2 PH3

[17] Some other metal phosphides could be used including aluminium phosphide, or calcium phosphide. Pure samples of phosphine, free from P2H4, may be prepared using the action of potassium hydroxide on phosphonium iodide:

[PH4]I + KOH → PH3 \+ KI + H2O

### Occurrence

[edit]

Phosphine is a worldwide constituent of the Earth's atmosphere at very low and highly variable concentrations.[18] It may contribute significantly to the global phosphorus biochemical cycle. The most likely source is reduction of phosphate in decaying organic matter, possibly via partial reductions and disproportionations, since environmental systems do not have known reducing agents of sufficient strength to directly convert phosphate to phosphine.[19]

It is also found in Jupiter's atmosphere.[20]

#### Possible extraterrestrial biosignature

[edit]

See also: Life on Venus

In 2020 a spectroscopic analysis was reported to show signs of phosphine in the atmosphere of Venus in quantities that could not be explained by known abiotic processes.[21][22][23] Later re-analysis of this work showed interpolation errors had been made, and re-analysis of data with the fixed algorithm do not result in the detection of phosphine.[24][25] The authors of the original study then claimed to detect it with a much lower concentration of 1 ppb.[26][disputed – discuss]

## Applications

[edit]

### Organophosphorus chemistry

[edit]

Phosphine is a precursor to many organophosphorus compounds. It reacts with formaldehyde in the presence of hydrogen chloride to give tetrakis(hydroxymethyl)phosphonium chloride, which is used in textiles. The hydrophosphination of alkenes is versatile route to a variety of phosphines. For example, in the presence of basic catalysts PH3 adds of Michael acceptors. Thus with acrylonitrile, it reacts to give tris(cyanoethyl)phosphine:[27]

PH3 \+ 3 CH2=CHZ → P(CH2CH2Z)3 (Z is NO2, CN, or C(O)NH2)

Acid catalysis is applicable to hydrophosphination with isobutylene and related analogues:

PH3 \+ R2C=CH2 → R2(CH3)CPH2

where R is CH3, alkyl, etc.

### Microelectronics

[edit]

Phosphine is used as a dopant in the semiconductor industry, and a precursor for the deposition of compound semiconductors. Commercially significant products include gallium phosphide and indium phosphide.[28]

### Fumigant (pest control)

[edit]

See also: Fumigation

Phosphine is an attractive fumigant because it is lethal to insects and rodents, but degrades to phosphoric acid, which is non-toxic. As sources of phosphine, for farm use, pellets of aluminium phosphide (AlP), calcium phosphide (Ca3P2), or zinc phosphide (Zn3P2) are used. These phosphides release phosphine upon contact with atmospheric water or rodents' stomach acid. These pellets also contain reagents to reduce the potential for ignition or explosion of the released phosphine.

An alternative is the use of phosphine gas itself which requires dilution with either CO2 or N2 or even air to bring it below the flammability point. Use of the gas avoids the issues related with the solid residues left by metal phosphide and results in faster, more efficient control of the target pests.

One problem with phosphine fumigants is the increased resistance by insects.[29]

## Toxicity and safety

[edit]

Further information: Aluminium phosphide poisoning

See also: White phosphorus munitions

Deaths have resulted from accidental exposure to fumigation materials containing aluminium phosphide or phosphine.[30][31][32][33] It can be absorbed either by inhalation or transdermally.[30] As a respiratory poison, it affects the transport of oxygen or interferes with the utilization of oxygen by various cells in the body.[32] Exposure results in pulmonary edema (the lungs fill with fluid).[33] Phosphine gas is heavier than air so it stays near the floor.[34]

Phosphine appears to be mainly a redox toxin, causing cell damage by inducing oxidative stress and mitochondrial dysfunction.[35] Resistance in insects is caused by a mutation in a mitochondrial metabolic gene.[29]

Phosphine can be absorbed into the body by inhalation. The main target organ of phosphine gas is the respiratory tract.[36] According to the 2009 U.S. National Institute for Occupational Safety and Health (NIOSH) pocket guide, and U.S. Occupational Safety and Health Administration (OSHA) regulation, the 8 hour average respiratory exposure should not exceed 0.3 ppm. NIOSH recommends that the short term respiratory exposure to phosphine gas should not exceed 1 ppm. The Immediately Dangerous to Life or Health level is 50 ppm. Overexposure to phosphine gas causes nausea, vomiting, abdominal pain, diarrhea, thirst, chest tightness, dyspnea (breathing difficulty), muscle pain, chills, stupor or syncope, and pulmonary edema.[37][38] Phosphine has been reported to have the odor of decaying fish or garlic at concentrations below 0.3 ppm. The smell is normally restricted to laboratory areas or phosphine processing since the smell comes from the way the phosphine is extracted from the environment. However, it may occur elsewhere, such as in industrial waste landfills. Exposure to higher concentrations may cause olfactory fatigue.[39]

### Fumigation hazards

[edit]

Phosphine is used for pest control, but its usage is strictly regulated due to high toxicity.[40][41] Gas from phosphine has high mortality rate[42] and has caused deaths in Sweden and other countries.[43][44][45]

Because the previously popular fumigant methyl bromide has been phased out in some countries under the Montreal Protocol, phosphine is the only widely used, cost-effective, rapidly acting fumigant that does not leave residues on the stored product. Pests with high levels of resistance toward phosphine have become common in Asia, Australia and Brazil. High level resistance is also likely to occur in other regions, but has not been as closely monitored. Genetic variants that contribute to high level resistance to phosphine have been identified in the dihydrolipoamide dehydrogenase gene.[29] Identification of this gene now allows rapid molecular identification of resistant insects.

### Explosiveness

[edit]

Phosphine gas is denser than air and hence may collect in low-lying areas. It can form explosive mixtures with air, and may also self-ignite.[12]

## In fiction

[edit]

Anne McCaffrey's Dragonriders of Pern series features genetically engineered dragons that breathe fire by producing phosphine by extracting it from minerals of their native planet.

In the 2008 pilot of the crime drama television series Breaking Bad, Walter White poisons two rival gangsters by adding red phosphorus to boiling water to produce phosphine gas. However, this reaction in reality would require white phosphorus instead, and for the water to contain sodium hydroxide.[46]

## See also

[edit]

* Diphosphane, H2P−PH2, simplified to P2H4
* Diphosphene, HP=PH

## Notes

[edit]

1. ^ For further information about the early history of phosphine, see:
* The Encyclopædia Britannica (1911 edition), vol. 21, p. 480: Phosphorus: Phosphine. Archived 4 November 2015 at the Wayback Machine
* Thomas Thomson, A System of Chemistry, 6th ed. (London, England: Baldwin, Cradock, and Joy, 1820), vol. 1, p. 272. Archived 4 November 2015 at the Wayback Machine
2. ^ Note:
* On p. 222 Archived 24 April 2017 at the Wayback Machine of his Traité élémentaire de chimie, vol. 1, (Paris, France: Cuchet, 1789), Lavoisier calls the compound of phosphorus and hydrogen "phosphure d'hydrogène" (hydrogen phosphide). However, on p. 216 Archived 24 April 2017 at the Wayback Machine, he calls the compound of hydrogen and phosphorus "Combinaison inconnue." (unknown combination), yet in a footnote, he says about the reactions of hydrogen with sulfur and with phosphorus: "Ces combinaisons ont lieu dans l'état de gaz & il en résulte du gaz hydrogène sulfurisé & phosphorisé." (These combinations occur in the gaseous state, and there results from them sulfurized and phosphorized hydrogen gas.)
* In Robert Kerr's 1790 English translation of Lavoisier's Traité élémentaire de chimie ... — namely, Lavoisier with Robert Kerr, trans., Elements of Chemistry ... (Edinburgh, Scotland: William Creech, 1790) — Kerr translates Lavoisier's "phosphure d'hydrogène" as "phosphuret of hydrogen" (p. 204), and whereas Lavoisier — on p. 216 of his Traité élémentaire de chimie ... — gave no name to the combination of hydrogen and phosphorus, Kerr calls it "hydruret of phosphorus, or phosphuret of hydrogen" (p. 198). Lavoisier's note about this compound — "Combinaison inconnue." — is translated: "Hitherto unknown." Lavoisier's footnote is translated as: "These combinations take place in the state of gas, and form, respectively, sulphurated and phosphorated oxygen gas." The word "oxygen" in the translation is an error because the original text clearly reads "hydrogène" (hydrogen). (The error was corrected in subsequent editions.)
3. ^ In 1857, August Wilhelm von Hofmann announced the synthesis of organic compounds containing phosphorus, which he named "trimethylphosphine" and "triethylphosphine", in analogy with "amine" (organo-nitrogen compounds), "arsine" (organo-arsenic compounds), and "stibine" (organo-antimony compounds).

## References

[edit]

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22. ^ Chu, Jennifer (18 December 2019). "A sign that aliens could stink". MIT News. Archived from the original on 18 February 2021. Retrieved 14 September 2020.
23. ^ "Phosphine Could Signal Existence of Alien Anaerobic Life on Rocky Planets". Sci-News. 26 December 2019. Archived from the original on 14 September 2020. Retrieved 15 September 2020.
24. ^ Snellen, I. A. G.; Guzman-Ramirez, L.; Hogerheijde, M. R.; Hygate, A. P. S.; van der Tak, F. F. S. (2020). "Re-analysis of the 267-GHz ALMA observations of Venus No statistically significant detection of phosphine". Astronomy and Astrophysics. 644: L2. arXiv:2010.09761. Bibcode:2020A&A...644L...2S. doi:10.1051/0004-6361/202039717. S2CID 224803085.
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27. ^ Trofimov, Boris A.; Arbuzova, Svetlana N.; Gusarova, Nina K. (1999). "Phosphine in the Synthesis of Organophosphorus Compounds". Russian Chemical Reviews. 68 (3): 215–227\. Bibcode:1999RuCRv..68..215T. doi:10.1070/RC1999v068n03ABEH000464. S2CID 250775640.
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## Further reading

[edit]

* Fluck, E. (1973). "The Chemistry of Phosphine". Topics in Current Chemistry. Fortschritte der Chemischen Forschung. 35: 1–64\. doi:10.1007/BFb0051358. ISBN 3-540-06080-4. S2CID 91394007.
* World Health Organization (1988). Phosphine and Selected Metal Phosphides. Environmental Health Criteria. Vol. 73\. Geneva: Joint sponsorship of UNEP, ILO and WHO.

## External links

[edit]

Wikimedia Commons has media related to Phosphine.

* International Chemical Safety Card 0694
* CDC – Phosphine – NIOSH Workplace Safety and Health Topic

* v
* t
* e

* Agents used in chemical warfare
* incapacitation
* riot control

Blood agents|

* Cyanogen
* Cyanogen bromide
* Cyanogen chloride (CK)
* Hydrogen cyanide (AC)
* Arsine
* Cacodyl cyanide
* Cacodyl oxide
* Hydrogen sulfide
* Phosphine
* Carbon monoxide
* Phosphorus trifluoride
* Methyl cyanoformate
* Iron pentacarbonyl
* Nickel tetracarbonyl
* 2,3,7,8-Tetrachlorodibenzodioxin
* Glycolonitrile
* Lactonitrile
* Acetone cyanohydrin
* Stibine
* Chloral cyanohydrin

Blister agents|

| Arsenicals|

* Ethyldichloroarsine (ED)
* Methyldichloroarsine (MD)
* Phenyldichloroarsine (PD)
* Lewisite (L)
* Lewisite 2 (L2)
* Lewisite 3 (L3)

|

Sulfur mustards|

* Levinstein mustard (EA-229)
* T
* Q
* CEES

Nitrogen mustards|

* HN1
* HN2
* HN3
* TL-301

Nettle agents|

* Phosgene oxime (CX)

Other|

* KB-16
* Dibutylchloromethyltin chloride
* Selenium oxychloride
* Phenacyl bromide
* Dimethyl acetylenedicarboxylate
* Dimethyl fumarate
* Chalcone hydrazone
* Methylnitronitrosoguanidine
* Norcantharidin
* Cantharidin
* T-2 mycotoxin

Nerve agents|

| G-agents|

* Tabun (GA)
* Sarin (GB)
* Chlorosarin (ClGB)
* Thiosarin (SGB)
* Soman (GD)
* Chlorosoman (ClGD)
* Ethylsarin (GE)
* GH
* Cyclosarin (GF)
* GP
* Fluorotabun
* EA-1356
* EA-4352
* Crotylsarin

|

V-agents|

* EA-2192
* EA-3148
* VE
* VG
* VM
* VP
* VR
* VS
* VX
* EA-1763
* Chinese VX
* V-sub x (GD-7)

GV agents|

* GV (EA-5365)

Novichok agents|

* A-208
* A-232
* A-234
* A-242
* A-262
* C01-A035
* C01-A039
* C01-A042

Carbamates|

* Dimethylcarbamoyl fluoride
* EA-3887
* EA-3887A
* EA-3966
* EA-3990
* EA-4056
* T-1123
* T-1152
* T-1194
* Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)
* TL-599
* TL-1238
* TL-1299
* TL-1317
* Miotine (AR-28/T-1843)
* 3152 CT
* 4-686-293-01 (Agent 1-10)

Other|

* Diisopropyl fluorophosphate
* Dicyclohexyl phosphorofluoridate
* EA-2012
* EA-2054
* EA-2098
* EA-2613
* 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate
* Neopentylene fluorophosphate
* Selenophos
* Phospholine
* R-16661
* Ro 3-0422
* Methanesulfonyl fluoride
* Dimefox (TL-792)
* MSPI

Precursors|

* Acetonitrile
* AT
* ATO
* AlP
* A.P.C. complex
* Chlorosarin
* Chlorosoman
* Cyclohexanol
* 1,8-Dibromooctane
* N,N-Diisopropylaminoethanol (KB)
* EA-1250
* DIHP
* ZS
* DEHP
* EA-1224
* Dimethylamidophosphoric dichloride
* Dimethylamidophosphoric dicyanide
* DMHP
* Ethylphosphonoselenoic dichloride
* Formaldoxime
* Nital
* 4-Hydroxycoumarin
* Isopropyl alcohol (TB)
* Methyldichlorophosphine (SW)
* Methylphosphonyl difluoride (difluoro) (DF)
* Methylphosphonyl dichloride (dichloro)
* Nitromethane
* OPA mixture
* Phosphoryl chloride
* Phosphorus pentachloride
* Phosphorus trichloride (TH)
* Pinacolone
* Pinacolyl alcohol
* Phenacyl chloride
* QL
* QL sulfide
* 2,4,5-Trichlorophenol
* 3,3,5-Trimethylcyclohexanol
* Triethyl phosphite
* Trimethyl phosphite
* TC
* TG

Neurotoxins|

* Anatoxin-a
* Saxitoxin (TZ)
* Coniine
* Bungarotoxin
* Botulinum toxin (BTX)
* Tetanospasmin (TeNT)
* Ryanodine
* Ciguatoxin (CTX)
* Guanitoxin (GTX)
* Chlorophenylsilatrane
* Palytoxin (PTX)
* Maitotoxin (MTX)
* Tetrodotoxin
* Veratridine
* Aconitine
* Brevetoxin (PbTX)
* Strychnine
* Antillatoxin (ATX)
* Tetraethyllead
* Dimethylmercury
* HN1 hydrochloride
* HN2 hydrochloride
* HN3 hydrochloride
* A-8564
* Picrotoxin
* Gelsemine
* Sulfuryl fluoride
* Tremorine
* Oxotremorine
* Batrachotoxin
* Tetramethylenedisulfotetramine (TETS)
* Bicyclic phosphates
* IPTBO
* TBPO
* TBPS
* Cloflubicyne
* Trimethylolpropane phosphite
* Domoic acid

Pulmonary/
choking agents|

* Chlorine
* Bromine
* Phosgene (CG)
* Fluorine
* Perfluoroisobutene
* Chloropicrin (PS)
* Dimethyl(trifluoromethylthio)arsine
* Diphosgene (DP)
* Disulfur decafluoride (Z)
* Acrolein
* Ethyl bromoacetate
* Perchloromethyl mercaptan
* Phenylcarbylamine chloride
* Tetranitromethane
* Tetrachlorodinitroethane
* Chlorine trifluoride
* Perchloryl fluoride
* Cadmium oxide
* Cadmium chloride
* Mercuric chloride
* Selenium dioxide
* Selenoyl fluoride
* Trifluoronitrosomethane
* Trichloronitrosomethane
* Nitric oxide
* Nitrogen dioxide
* Dinitrogen tetroxide
* Sulfur dioxide
* Phosphorus trichloride
* Methyl isocyanate
* Ethenone
* Methyl vinyl ketone
* Trifluoroacetyl chloride
* Salcomine
* Fluomine
* Uranium hexafluoride
* Diborane
* Green Cross

Vomiting agents|

* Adamsite (DM)
* Chloropicrin
* Litharge-glycerine
* Diphenylchlorarsine
* Diphenylcyanoarsine
* Cacodyl cyanide
* o-Dianisidine
* Antimony potassium tartrate
* Lobeline

Incapacitating
agents|

* BZ (CS-4030)
* Apomorphine
* Butyrophenone
* EA-4941 (CS-4640)
* Etorphine
* EA-2092
* CS-4297
* Etoxadrol
* Dimethylheptylpyran (DMHP)
* Canbisol
* EA-2148
* EA-3167
* Nicotine
* EA-3443
* Methaqualone
* Pethidine
* EA-3580
* Ibogaine
* EA-3834
* Kolokol-1
* LSD-25
* PAVA spray
* Psilocybin
* Sleeping gas
* Carfentanil
* JB-318
* JB-336
* CS-27349
* CAR-226,086
* CAR-301,060
* CAR-302,196
* CAR-302,282
* CAR-302,668
* Benperidol
* Desflurane
* Enflurane
* Bufotenin
* Isoflurane
* Halothane
* Sevoflurane
* Pentazocine
* Procarbazine
* Fluphenazine
* Chlorpromazine

Lachrymatory
agents|

* Xylyl bromide
* Pepper spray (OC)
* Mace (spray)
* Phorbol esters
* Ingenol mebutate
* RTX
* CN
* CS
* CR
* CNS
* Benzyl chloride
* Benzyl bromide
* Benzyl iodide
* Bromobenzyl cyanide
* Thiophosgene
* Chloroacetone
* Bromoacetone
* Bromomethyl ethyl ketone
* Acrolein
* Phenacyl bromide
* Chloroacetophenone oxime
* Ethyl bromoacetate
* Ethyl iodoacetate
* Iodoacetone
* Allyl isothiocyanate
* Hexamethylene diisocyanate
* Crotonaldehyde
* Croton oil
* DRC-5593

Malodorant agents|

* Thioacetone
* Allicin
* Skatole
* Cadaverine
* Putrescine

Cornea-clouding agents|

* Lewisite
* CX
* KB-16
* Methyl cyanoacrylate
* N-Methylmorpholine
* Allyl alcohol
* Osmium tetroxide
* Acrolein
* Cacodyl cyanide
* Diglycolic acid esters

Biological toxins|

* Abrin
* Aconitine
* Cyclopiazonic acid
* Histrionicotoxins
* Aflatoxins
* Anatoxin-a
* Batrachotoxin
* Botulinum toxin
* Brevetoxin
* Ciguatoxin
* Domoic acid
* Enterotoxin type B
* Grayanotoxin
* Guanitoxin
* Maitotoxin
* Modeccin
* Palytoxin
* Ricin
* Saxitoxin
* Shiga toxin
* T-2 mycotoxin
* Tetanospasmin
* Tetrodotoxin
* Volkensin
* Veratridine

Tumor promoting agents|

* Phorbol esters
* 12-O-Tetradecanoylphorbol-13-acetate
* Croton oil

Other|

* Methyl fluoroacetate
* Napalm (variants and mixtures)
* Fluoroethyl fluoroacetate
* Depleted uranium
* post-combustion uranium oxides
* Plutonium and its compounds
* Polonium
* White phosphorus

* List of chemical warfare agents
* CB military symbol

* v
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* e

Phosphorus compounds

Phosphides|

* AlP
* AsP
* BP
* BiP
* Cs2P5
* Ca3P2
* Cd3P2
* Cu3P
* DyP
* ErP
* EuP
* GdP
* AuP
* FeP
* Fe3P
* HfP
* HoP
* InP
* LaP
* Li3P
* LuP
* MoP
* MoP2
* Mo3P
* NbP
* NdP
* NpP
* Np3P4
* OsP2
* Ru2P
* PtP2
* PrP
* PrP5
* PuP
* ScP
* SmP
* SmP5
* Sr3P2
* TbP
* SnP3
* ThP7
* TmP
* YP
* YbP
* ZnP2
* Zn3P2
* ZrP
* ZrP2

Other compounds|

* PBr3
* PBr5
* PBr7
* PCl3
* PCl5
* P2Cl4
* PF3
* PF5
* PI3
* PH3
* PN
* P3N5
* PO
* P2O3
* P2O4
* P2O5
* P4S3
* P4Sx
* P4S10

* v
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Phosphides

Binary phosphides|

| PH3 |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |  | He

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Li3P | Be  |  |  |  |  |  |  |  |  |  |  |  | BP | CP
+C | N  | +O | F  | Ne
Na3P | Mg3P2 |  |  |  |  |  |  |  |  |  |  |  | AlP | +Si
-SiP | P | S  | +Cl | Ar
K3P | CaP
Ca3P2 |  | ScP | TiP | V  | CrP
Cr3P | Mn  | FeP
Fe3P | CoP
Co2P
Co3P2 | NixPy | Cu3P | Zn3P2
ZnP2 | GaP | -GeP | AsP | Se  | +Br | Kr
Rb  | Sr3P2 |  | YP | ZrP
ZrP2 | NbP | MoP
MoP2
Mo3P | Tc  | Ru2P | Rh  | Pd  | Ag3P | Cd3P2 | InP | SnP3 | SbP | +Te | +I | Xe
CsxPy | Ba  | *  | LuP | HfP | Ta  | W  | Re  | OsP2 | Ir  | PtP2 | Au2P3 | Hg  | Tl  | PbP7 | BiP | Po  | At  | Rn
Fr  | Ra  | **  | Lr  | Rf  | Db  | Sg  | Bh  | Hs  | Mt  | Ds  | Rg  | Cn  | Nh  | Fl  | Mc  | Lv  | Ts  | Og
|  | ↓  |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
|  | * | LaP | CeP | PrP
PrP5 | NdP | Pm  | SmP
SmP5 | EuP | GdP | TbP | DyP | HoP | ErP | TmP | YbP |  |
|  | ** | AcP | ThP7 | Pa  | UP | NpP
Np3P4 | PuP | Am  | Cm  | BkP | Cf  | Es  | Fm  | Md  | No  |  |

Ternary phosphides|

* GaInP
* GaAsP
* AlGaP

Quaternary phosphides|

* Zn-Cd-P-As
* InAsSbP
* AlGaInP

Quinary phosphides|

* GaInAsSbP

See also|

* Ferrophosphorus

* v
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Molecules detected in outer space

Molecules|

| Diatomic|

* Aluminium monochloride
* Aluminium monofluoride
* Aluminium(II) oxide
* Argonium
* Carbon cation
* Carbon monophosphide
* Carbon monosulfide
* Carbon monoxide
* Cyano radical
* Diatomic carbon
* Fluoromethylidynium
* Helium hydride ion
* Hydrogen chloride
* Hydrogen fluoride
* Hydrogen (molecular)
* Hydroxyl radical
* Imidogen
* Iron(II) oxide
* Magnesium monohydride
* Methylidyne radical
* Nitric oxide
* Nitrogen (molecular)
* Oxygen (molecular)
* Phosphorus monoxide
* Phosphorus mononitride
* Potassium chloride
* Silicon carbide
* Silicon monoxide
* Silicon monosulfide
* Sodium chloride
* Sodium iodide
* Sulfanyl
* Sulfur mononitride
* Sulfur monoxide
* Titanium(II) oxide

|
|

Triatomic|

* Aluminium(I) hydroxide
* Aluminium isocyanide
* Amino radical
* Carbon dioxide
* Carbonyl sulfide
* CCP radical
* Chloronium
* Diazenylium
* Dicarbon monoxide
* Disilicon carbide
* Ethynyl radical
* Formyl radical
* Hydrogen cyanide (HCN)
* Hydrogen isocyanide (HNC)
* Hydrogen sulfide
* Hydroperoxyl
* Iron cyanide
* Isoformyl
* Magnesium cyanide
* Magnesium isocyanide
* Methylene
* Methylidynephosphane
* N2H+
* Nitrous oxide
* Nitroxyl
* Ozone
* Potassium cyanide
* Sodium cyanide
* Sodium hydroxide
* Silicon carbonitride
* c-Silicon dicarbide
* SiNC
* Sulfur dioxide
* Thioformyl
* Thioxoethenylidene
* Titanium dioxide
* Tricarbon
* Trihydrogen cation
* Water

Four
atoms|

* Acetylene
* Ammonia
* Cyanoethynyl
* Formaldehyde
* Fulminic acid
* HCCN
* Hydrogen peroxide
* Hydromagnesium isocyanide
* Isocyanic acid
* Isothiocyanic acid
* Ketenyl
* Methyl cation
* Methyl radical
* Methylene amidogen
* Propynylidyne
* Protonated carbon dioxide
* Protonated hydrogen cyanide
* Silicon tricarbide
* Thiocyanic acid
* Thioformaldehyde
* Tricarbon monosulfide
* Tricarbon monoxide

Five
atoms|

* Ammonium ion
* Butadiynyl
* Carbodiimide
* Cyanamide
* Cyanoacetylene
* Cyanoformaldehyde
* Cyanomethyl
* Cyclopropenylidene
* Formic acid
* Isocyanoacetylene
* Ketene
* Methane
* Methoxy radical
* Methylenimine
* Propadienylidene
* Protonated formaldehyde
* Silane
* Silicon-carbide cluster

Six
atoms|

* Acetonitrile
* Cyanobutadiynyl radical
* Cyclopropenone
* Diacetylene
* E-Cyanomethanimine
* Ethylene
* Formamide
* HC4N
* Ketenimine
* Methanethiol
* Methanol
* Methyl isocyanide
* Pentynylidyne
* Propynal
* Protonated cyanoacetylene

Seven
atoms|

* Acetaldehyde
* Acrylonitrile
* Vinyl cyanide
* Cyanodiacetylene
* Ethylene oxide
* Glycolonitrile
* Hexatriynyl radical
* Methyl isocyanate
* Methylamine
* Propyne
* Vinyl alcohol

Eight
atoms|

* Acetic acid
* Acrolein
* Aminoacetonitrile
* Cyanoallene
* Ethanimine
* Glycolaldehyde
* Hexapentaenylidene
* Methyl formate
* Methylcyanoacetylene

Nine
atoms|

* Acetamide
* Cyanohexatriyne
* Dimethyl ether
* Ethanethiol
* Ethanol
* Methyldiacetylene
* N-Methylformamide
* Octatetraynyl radical
* Propene
* Propionitrile

Ten
atoms
or more|

* Acetone
* Benzene
* Benzonitrile
* Buckminsterfullerene (C60, C60+, fullerene, buckyball)
* Butyronitrile
* C70 fullerene
* Cyanodecapentayne
* Ethyl formate
* Ethylene glycol
* Heptatrienyl radical
* Methyl acetate
* Methyl-cyano-diacetylene
* Methyltriacetylene
* Propionaldehyde
* Pyrimidine

Deuterated
molecules|

* Ammonia
* Ammonium ion
* Formaldehyde
* Formyl radical
* Heavy water
* Hydrogen cyanide
* Hydrogen deuteride
* Hydrogen isocyanide
* N2D+
* Propyne
* Trihydrogen cation

Unconfirmed|

* Anthracene
* Dihydroxyacetone
* Glycine
* Graphene
* H2NCO+
* Hemolithin
* Linear C5
* Methoxyethane
* Naphthalene cation
* Phosphine
* Pyrene
* Silylidyne

Related|

* Abiogenesis
* Astrobiology
* Astrochemistry
* Atomic and molecular astrophysics
* Chemical formula
* Circumstellar dust
* Circumstellar envelope
* Cosmic dust
* Cosmic ray
* Cosmochemistry
* Diffuse interstellar band
* Earliest known life forms
* Extraterrestrial life
* Extraterrestrial liquid water
* Forbidden mechanism
* Homochirality
* Intergalactic dust
* Interplanetary medium
* Interstellar medium
* Iron–sulfur world theory
* Kerogen
* Molecules in stars
* Nexus for Exoplanet System Science
* Organic compound
* Outer space
* PAH world hypothesis
* Photodissociation region
* Polycyclic aromatic hydrocarbon (PAH)
* Pseudo-panspermia
* RNA world hypothesis
* Spectroscopy
* Tholin

* Category:Astrochemistry
* Outer space portal
* Astronomy portal
* Chemistry portal

* v
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* e

Binary compounds of hydrogen

Alkali metal
(Group 1) hydrides|

* LiH
* NaH
* KH
* RbH
* CsH

Alkaline (Group 2)
earth hydrides|

| Monohydrides|

* BeH
* MgH
* CaH
* SrH
* BaH

|

Dihydrides|

* BeH2
* MgH2
* CaH2
* SrH2
* BaH2

|

Group 13
hydrides|

| Boranes|

* BH3
* BH
* B2H6
* B2H2
* B2H4
* B4H10
* B5H9
* B5H11
* B6H10
* B6H12
* B10H14
* B18H22

|

Alanes|

* AlH3
* Al2H6

|

Gallanes|

* GaH3
* Ga2H6

|

Indiganes|

* InH3
* In2H6

|

Thallanes|

* TlH3
* Tl2H6

|

Nihonanes (predicted)|

* NhH
* NhH3
* Nh2H6
* NhH5

|

Group 14 hydrides|

| Hydrocarbons|

* alkanes
* alkenes
* alkynes
* Cycloalkanes
* Cycloalkenes
* Cycloalkynes
* Annulenes

|

* CH
* CH2
* CH3
* C2H

Silanes|

* SiH4
* Si2H6
* Si3H8
* Si4H10
* Si5H12
* Si6H14
* Si7H16
* Si8H18
* Si9H20
* Si10H22
* more...

|

Silenes|

* Si2H4

|

Silynes|

* Si2H2
* SiH

|

Germanes|

* GeH4
* Ge2H6
* Ge3H8
* Ge4H10
* Ge5H12

|

Stannanes|

* SnH4
* Sn2H6

|

Plumbanes|

* PbH4

|

Flerovanes (predicted)|

* FlH
* FlH2
* FlH4

|

Pnictogen
(Group 15) hydrides|

| Azanes|

* NH3
* N2H4
* N3H5
* N4H6
* N5H7
* N6H8
* N7H9
* N8H10
* N9H11
* N10H12
* more...

|

Azenes|

* N2H2
* N3H3
* N4H4

|

Phosphanes|

* PH3
* P2H4
* P3H5
* P4H6
* P5H7
* P6H8
* P7H9
* P8H10
* P9H11
* P10H12
* more...

|

Phosphenes|

* P2H2
* P3H3
* P4H4

|

Arsanes|

* AsH3
* As2H4

|

Stibanes|

* SbH3

|

Bismuthanes|

* BiH3

|

Moscovanes|

* McH3 (predicted)

|

* HN3
* NH
* HN5
* NH5 (hypothetical)

Hydrogen
chalcogenides
(Group 16 hydrides)|

| Polyoxidanes|

* H2O
* H2O2
* H2O3
* H2O4
* H2O5
* more...

|

Polysulfanes|

* H2S
* H2S2
* H2S3
* H2S4
* H2S5
* H2S6
* H2S7
* H2S8
* H2S9
* H2S10
* more...

|

Selanes|

* H2Se
* H2Se2

|

Tellanes|

* H2Te
* H2Te2

|

Polanes|

* PoH2

|

Livermoranes|

* LvH2 (predicted)

|

* HO
* HO2
* HO3
* H2O+–O– (hypothetical)
* H2S+-S-
* HS
* HS2
* HDO
* D2O
* T2O

Hydrogen halides
(Group 17 hydrides)|

* HF
* HCl
* HBr
* HI
* HAt
* HTs (predicted)

Transition
metal hydrides|

* ScH2
* YH2
* YH3
* YH6
* YH9
* LuH2
* LuH3
* TiH2
* TiH4
* ZrH2
* ZrH4
* HfH2
* HfH4
* VH
* VH2
* NbH
* NbH2
* TaH
* TaH2
* CrH
* CrH2
* CrHx
* FeH
* FeH2
* FeH5
* CoH2
* RhH2
* IrH3
* NiH
* PdHx (x < 1)
* PtHx (x< 1)
* DsH2 (predicted)
* CuH
* AgH
* AuH
* RgH (predicted)
* ZnH2
* CdH2
* HgH
* Hg2H2
* HgH2
* CnH2 (predicted)

Lanthanide
hydrides|

* LaH2
* LaH3
* LaH10
* CeH2
* CeH3
* PrH2
* PrH3
* NdH2
* NdH3
* SmH2
* SmH3
* EuH2
* GdH2
* GdH3
* TbH2
* TbH3
* DyH2
* DyH3
* HoH2
* HoH3
* ErH2
* ErH3
* TmH2
* TmH3
* YbH2
* LuH2
* LuH3

Actinide
hydrides|

* AcH2
* ThH2
* ThH4
* Th4H15
* PaH3
* UH3
* UH4
* NpH2
* NpH3
* PuH2
* PuH3
* AmH2
* AmH3
* CmH2
* BkH2
* BkH3
* CfH2
* CfH3

Exotic matter hydrides|

* PsH

Portals:

* Chemistry
* Stars
* Solar System
* Science

Authority control databases: National |

* Japan
* Czech Republic
* Israel

|

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